Dichloromethane → 5-Bromo-2,3-dimethoxypyridine

HRID 1162451

Reaction equation

HRID 1162451 reaction equation
[CH3:1][O:2][C:3]1[C:8]([O:9][CH3:10])=[CH:7][CH:6]=[CH:5][N:4]=1.C(Cl)Cl.[Br:14]Br>C([O-])(O)=O.[Na+]>[Br:14][C:6]1[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[N:4][CH:5]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 46578092,3-Dimethoxypyridine

Product 1

HCID 125630845-Bromo-2,3-dimethoxypyridineYield 64.9%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a 100 mL round-bottomed flask was added 2,3-dimethoxypyridine (2 mL, 15 mmol, Alfa Aesar, Ward Hill, Mass.), CH2Cl2 (30 mL), and bromine (0.7 mL, 14 mmol). The reaction mixture was stirred at rt for 16 h. The reaction mixture was then diluted with sat. NaHCO3 (30 mL) and extracted with EtOAc (2×50 mL). The combined organic extracts were washed with sat. NaCl (20 mL), dried over Na2SO4, filtered and concentrated. Purification by silica gel chromatography (50% CH2Cl2/hexanes) afforded the title compound (1.98 g, 60%). MS (ESI, positive ion) m/z: 218 (M(79Br)+1).

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. washThe combined organic extracts were washed with sat. NaCl (20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (50% CH2Cl2/hexanes)

Sources & evidence

ORD record
ord-08016a45d69e42e1b8eee1f95839037d
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Linked notes

Loading…